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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 3, pp 284–289 | Cite as

Behavior of dialkylallyl(4-hydroxybut-2-ynyl)ammonium bromides toward powdered sodium hydroxide and aqueous alkali

  • E. O. ChukhadjianEmail author
  • A. S. Gabrielyan
  • A. R. Gevorkyan
  • G. A. Panosyan
  • T. D. Karapetyan
Article

Under the influence of a twofold molar quantity of powdered sodium hydroxide in the presence of a few drops of methanol at room temperature dialkylallyl(4-hydroxybut-2-ynyl)ammonium bromides undergo a Stevens rearrangement with transfer of the reaction center, forming substituted amino alcohols with an allene group. Intramolecular cyclization of the products and concurrent hydration lead to the formation of a mixture of dialkyl(4-allyl-2,5-dihydrofuran-2-yl)amines and dialkylamino-3-allyl-4-hydroxybutanones with overall yields of 37-41%. During the aqueous-alkali cleavage of dialkylallyl(4-hydroxybut-2-ynyl)ammonium bromides the products from intramolecular cyclization were obtained with yields of 38-41%. Under the conditions both of Stevens rearrangement and of aqueous-alkali cleavage the secondary amines are also formed with yields of 15-17%. As nonamine products mixtures of compounds, which according to the IR spectra contain unconjugated and conjugated carbonyl groups, were obtained. The presence of an aldehyde group was established by a silver mirror reaction.

Keywords

dialkylallyl(4-hydroxybut-2-ynyl)ammonium bromides sodium hydroxide dialkyl(4-allyl-2,5-dihydrofuran-2-yl)amines intramolecular cyclization water-alkali cleavage Stevens rearrangement 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • E. O. Chukhadjian
    • 1
    Email author
  • A. S. Gabrielyan
    • 1
  • A. R. Gevorkyan
    • 1
  • G. A. Panosyan
    • 2
  • T. D. Karapetyan
    • 3
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanRepublic of Armenia
  2. 2.Molecular Structure Research Center National Academy of Sciences of the Republic of ArmeniaYerevanRepublic of Armenia
  3. 3.M. Heratsi Yerevan State Medical UniversityYerevanRepublic of Armenia

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